(R)-nonadec-1-en-4-ol | 307557-82-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (R)-nonadec-1-en-4-ol
• 英文别名: (4R)-nonadec-1-en-4-ol
• CAS: 307557-82-0
• 化学式: C₁₉H₃₈O
• 分子量: 282.51
• InChiKey: ZLGVCQXWYKJRPY-IBGZPJMESA-N

物化性质

• 沸点：
  376.7±11.0 °C(Predicted)
• 密度：
  0.842±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  20
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (R)-nonadec-1-en-4-ol 在 sodium chlorite 、 sodium dihydrogenphosphate 、 2-甲基-2-丁烯 、 水 、 臭氧 作用下， 以 吡啶 、 二氯甲烷 、 乙腈 、 叔丁醇 为溶剂， 反应 2.0h， 生成 (R)-3-hydroxyoctadecanoic acid
  参考文献：
  名称：

  基于对映选择性有机催化合成 3-羟基脂肪酸和脂肪 γ-内酯

  摘要：

  3-羟基脂肪酸引起了研究人员的兴趣，因为它们中的一些可能比非羟基化的对应物更有效地与游离脂肪酸受体相互作用，并且它们在血浆中的测定提供了有关线粒体缺陷的诊断信息。我们在此介绍了一种用于 3-羟基脂肪酸不对称合成的便捷通用方法的开发。从长链醛开始，末端环氧化物的对映选择性有机催化合成是我们方法的关键步骤，然后是用乙烯基溴化镁开环。臭氧分解和随后的氧化产生目标产物。MacMillan 的第三代咪唑啉酮有机催化剂已用于环氧化物的形成，确保产品具有高对映体纯度。此外，开发了一种在带有羟基的碳原子上掺入氘的途径，从而可以合成氘代衍生物，这可能有助于生物学研究和质谱研究。此外，还探索了与 4-羟基脂肪酸相对应的脂肪 γ-内酯的合成。

  DOI：

  10.3390/molecules24112081
• 作为产物：
  描述：

  十六醛 在 四氯化钛 、 对甲苯磺酸 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 、 苯 为溶剂， 生成 (R)-nonadec-1-en-4-ol
  参考文献：
  名称：

  Syntheses and biological evaluation of novel pseudomycin side-chain analogues. Part 2

  摘要：

  A series of aliphatic side-chain analogues of pseudomycin was synthesized and evaluated during the course of our sidechain SAR effort. We found that several of the pseudomycin side-chain analogues (e.g., 10) exhibited good in vitro activity against all three major fungi responsible for systemic fungal infections. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00424-8

文献信息

• Stereoselective Synthesis of the Antiprotozoal Lactone Passifloricin A and Seven Isomers Thereof
  作者：Juan Murga、Jorge García-Fortanet、Miguel Carda、J. Alberto Marco

  DOI：10.1021/jo049275d

  日期：2004.10.1

  The conjugated δ-lactone passifloricin A, a natural product with antiprotozoal activity, and seven isomers thereof have been synthesized in enantiopure form. It has been shown in this way that the proposed structure for the natural compound was erroneous. The correct structure is now evidenced. Key steps of the syntheses were asymmetric Brown-type aldehyde allylations and ring-closing metatheses.

  具有对原生动物活性的天然产物共轭的δ-内酯西番莲菌素A及其七个异构体以对映体纯的形式合成。已经表明以这种方式提出的天然化合物的结构是错误的。现在证明了正确的结构。合成的关键步骤是不对称的布朗型醛烯丙基化和闭环复分解。
• Total Synthesis of Tetraketide and Cryptorigidifoliol I via a Sequential Allylation Strategy
  作者：Birakishore Padhi、G. Sudhakar Reddy、Debendra K. Mohapatra

  DOI：10.1021/acs.jnatprod.6b00443

  日期：2016.11.23

  cryptorigidifoliol I (2) has been devised successfully from commercially available starting materials in 11 and 17 steps, with 16% and 11% overall yields, respectively. Highlights of the syntheses involved sequential Lewis acid-catalyzed highly regio- and diastereoselective allylations and intramolecular Mitsunobu lactonization.

  已经从商业上可得的起始原料成功地为11步和17步设计了统一的高效合成四酮化合物（1）和隐秘三氟酚I（2）的合成路线，总收率分别为16％和11％。合成的亮点涉及连续的路易斯酸催化的高度区域和非对映选择性的烯丙基化和分子内光延内酯化。
• Total Synthesis and Structure Confirmation of Cryptocaryol A
  作者：D. Srinivas Reddy、Debendra K. Mohapatra

  DOI：10.1002/ejoc.201201309

  日期：2013.2

  The first enantioselective total synthesis of Pdcd4-stabilizing cryptocaryol A, a secondary metabolite obtained from a tropical tree, has been achieved through an iterative approach to the 1,3-polyol motif. The key steps are a Maruoka allylation, a Reetz chelation-controlled allylation with 1,3-induction, iterative diastereoselective iodocyclization, and ring-closing metathesis reactions.

  Pdcd4 稳定cryptocaryol A 的第一个对映选择性全合成是通过对1,3-多元醇基序的迭代方法实现的，它是一种从热带树中获得的次级代谢物。关键步骤是 Maruoka 烯丙基化、Reetz 螯合控制的 1,3 诱导烯丙基化、迭代非对映选择性碘环化和闭环复分解反应。
• On the Structure of Passifloricin A:  Asymmetric Synthesis of the δ-Lactones of (2<i>Z</i>,5<i>S</i>,7<i>R</i>,9<i>S</i>,11<i>S</i>)- and (2<i>Z</i>,5<i>R</i>,7<i>R</i>,9<i>S</i>,11<i>S</i>)-Tetrahydroxyhexacos-2-enoic Acid
  作者：Jorge García-Fortanet、Juan Murga、Miguel Carda、J. Alberto Marco

  DOI：10.1021/ol034182o

  日期：2003.5.1

  graphicStereoselective syntheses of the delta-lactone of (2Z,5S,7R,9S,11S)-tetrahydroxyhexacos-2-enoic acid, the structure reported for passifloricin A, and of its (5R)-epimer are described. The creation of all stereogenic centers relied upon Brown's asymmetric allylation methodology. The lactone ring was created via ring-closing metathesis. The NMR data of both synthetic products, however, were different from those of the natural product. The published structure of passifloricin A is thus erroneous and will require further synthetic work to be unambiguously assigned.
• Antiparasite and antimycobacterial activity of passifloricin analogues
  作者：Wilson Cardona、Winston Quiñones、Sara Robledo、Ivan Darío Vélez、Juan Murga、Jorge García-Fortanet、Miguel Carda、Diana Cardona、Fernando Echeverri

  DOI：10.1016/j.tet.2006.02.017

  日期：2006.4

  Several structural analogues of the polyketide passifloricin lactone were synthesized using asymmetric stereoselective allylations and ring-closing methateses as key reactions. These compounds were active in vitro against intracellular amastigotes of Leishmania panamensis (strain UA 140), trophozoites of Plasinodium falciparum (strain NF54), and Mycobacterium tuberculosis (strain H(37)Rv). However, in spite of the significative antiparasitic activity of some synthetic analogues a high cytotoxicity was also observed. Based on these results a lactam derivative was also synthesized. This compound maintained a good level of activity with less toxicity. (c) 2006 Elsevier Ltd. All fights reserved.